JP6561055B2 - 三環式イミダゾール化合物 - Google Patents
三環式イミダゾール化合物 Download PDFInfo
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- JP6561055B2 JP6561055B2 JP2016532102A JP2016532102A JP6561055B2 JP 6561055 B2 JP6561055 B2 JP 6561055B2 JP 2016532102 A JP2016532102 A JP 2016532102A JP 2016532102 A JP2016532102 A JP 2016532102A JP 6561055 B2 JP6561055 B2 JP 6561055B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- pyridin
- oxoethoxy
- imidazo
- hexahydroimidazo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000002460 imidazoles Chemical class 0.000 title description 3
- -1 dimethylcarbamoyl Chemical group 0.000 claims description 589
- 125000000217 alkyl group Chemical group 0.000 claims description 211
- 150000001875 compounds Chemical class 0.000 claims description 210
- 238000000034 method Methods 0.000 claims description 135
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 98
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 94
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 84
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 82
- 125000001424 substituent group Chemical group 0.000 claims description 77
- 229920006395 saturated elastomer Polymers 0.000 claims description 72
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 42
- 229940076279 serotonin Drugs 0.000 claims description 34
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 26
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 25
- 208000035475 disorder Diseases 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 10
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
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- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 5
- RVQSTBUBISLSAL-UHFFFAOYSA-N 2-(2-chloro-4-morpholin-4-ylphenoxy)-1-[3-(4-cyclopropyl-2-fluorophenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]ethanone Chemical compound ClC1=C(OCC(=O)N2C(C3=C(N=C4N3CCNC4)CC2)C2=C(C=C(C=C2)C2CC2)F)C=CC(=C1)N1CCOCC1 RVQSTBUBISLSAL-UHFFFAOYSA-N 0.000 claims description 5
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
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- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 4
- IZWAKOKJYQJGGZ-UHFFFAOYSA-N 5-[4-[2-(2-chloro-6-morpholin-4-ylpyridin-3-yl)oxyacetyl]-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-3-yl]-N,N-dimethylthiophene-3-carboxamide Chemical compound ClC1=NC(=CC=C1OCC(=O)N1C(C2=C(N=C3N2CCNC3)CC1)C1=CC(=CS1)C(=O)N(C)C)N1CCOCC1 IZWAKOKJYQJGGZ-UHFFFAOYSA-N 0.000 claims description 4
- AJWQNPGMDHMAHZ-UHFFFAOYSA-N N-[5-[2-[12-(4-chloro-2-fluorophenyl)-5-thia-2,7,11-triazatricyclo[6.4.0.02,6]dodeca-1(8),6-dien-11-yl]-2-oxoethoxy]-6-ethylpyridin-2-yl]methanesulfonamide Chemical compound ClC1=CC(=C(C=C1)C1N(CCC2=C1N1C(=N2)SCC1)C(COC=1C=CC(=NC=1CC)NS(=O)(=O)C)=O)F AJWQNPGMDHMAHZ-UHFFFAOYSA-N 0.000 claims description 4
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 4
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 4
- 230000004064 dysfunction Effects 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 239000012634 fragment Substances 0.000 claims description 4
- 201000011519 neuroendocrine tumor Diseases 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- UDQFXQSXCRMUFX-UHFFFAOYSA-N 1-[11-acetyl-3-(4-cyclopropyl-2-fluorophenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-(2-chloro-4-morpholin-4-ylphenoxy)ethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N2)CCN(C1C1=C(C=C(C=C1)C1CC1)F)C(COC1=C(C=C(C=C1)N1CCOCC1)Cl)=O UDQFXQSXCRMUFX-UHFFFAOYSA-N 0.000 claims description 3
- GYLREMMSRHRSLL-UHFFFAOYSA-N 2-(2-chloro-4-morpholin-4-ylphenoxy)-1-[3-(4-cyclopropyl-2-fluorophenyl)-11-(cyclopropylmethyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]ethanone Chemical compound ClC1=C(OCC(=O)N2C(C3=C(N=C4N3CCN(C4)CC4CC4)CC2)C2=C(C=C(C=C2)C2CC2)F)C=CC(=C1)N1CCOCC1 GYLREMMSRHRSLL-UHFFFAOYSA-N 0.000 claims description 3
- JWDVPKCZZCBQFT-UHFFFAOYSA-N 5-[11-acetyl-4-[2-(2-chloro-6-morpholin-4-ylpyridin-3-yl)oxyacetyl]-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-3-yl]-N,N-dimethylthiophene-3-carboxamide Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=CC(=CS1)C(=O)N(C)C)C(COC=1C(=NC(=CC=1)N1CCOCC1)Cl)=O JWDVPKCZZCBQFT-UHFFFAOYSA-N 0.000 claims description 3
- 206010000060 Abdominal distension Diseases 0.000 claims description 3
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- 208000015943 Coeliac disease Diseases 0.000 claims description 3
- 206010010774 Constipation Diseases 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 208000009139 Gilbert Disease Diseases 0.000 claims description 3
- 208000022412 Gilbert syndrome Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 3
- 206010028813 Nausea Diseases 0.000 claims description 3
- 206010035664 Pneumonia Diseases 0.000 claims description 3
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 3
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 3
- 206010040108 Serotonin syndrome Diseases 0.000 claims description 3
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
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- MAGVNHMYTDXKOO-UHFFFAOYSA-N 1-[11-acetyl-3-(2,4-dimethyl-1,3-thiazol-5-yl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-[2-chloro-6-(1,3-oxazol-2-yl)pyridin-3-yl]oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=C(N=C(S1)C)C)C(COC=1C(=NC(=CC=1)C=1OC=CN=1)Cl)=O MAGVNHMYTDXKOO-UHFFFAOYSA-N 0.000 claims description 2
- LKKNPZBEHUYBJA-UHFFFAOYSA-N 1-[11-acetyl-3-(2-fluoro-4-methylphenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-[2-chloro-4-(morpholin-4-ylmethyl)phenoxy]ethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=C(C=C(C=C1)C)F)C(COC1=C(C=C(C=C1)CN1CCOCC1)Cl)=O LKKNPZBEHUYBJA-UHFFFAOYSA-N 0.000 claims description 2
- WYVPWWATXGAQFA-UHFFFAOYSA-N 1-[11-acetyl-3-(3-fluoropyridin-2-yl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-(2-chloro-6-morpholin-4-ylpyridin-3-yl)oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=NC=CC=C1F)C(COC=1C(=NC(=CC=1)N1CCOCC1)Cl)=O WYVPWWATXGAQFA-UHFFFAOYSA-N 0.000 claims description 2
- VOUPJWVPWSFRMC-UHFFFAOYSA-N 1-[11-acetyl-3-(3-fluorothiophen-2-yl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-(2-chloro-6-morpholin-4-ylpyridin-3-yl)oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C=1SC=CC=1F)C(COC=1C(=NC(=CC=1)N1CCOCC1)Cl)=O VOUPJWVPWSFRMC-UHFFFAOYSA-N 0.000 claims description 2
- RDDQOSWZNQQEII-UHFFFAOYSA-N 1-[11-acetyl-3-(4-chloro-2-fluorophenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-[2-chloro-6-(3,3-difluoroazetidin-1-yl)pyridin-3-yl]oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=C(C=C(C=C1)Cl)F)C(COC=1C(=NC(=CC=1)N1CC(C1)(F)F)Cl)=O RDDQOSWZNQQEII-UHFFFAOYSA-N 0.000 claims description 2
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- VINCCSXKCFGAGE-UHFFFAOYSA-N 1-[11-acetyl-3-(4-cyclopropyl-2-fluorophenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-(2-chloropyridin-3-yl)oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=C(C=C(C=C1)C1CC1)F)C(COC=1C(=NC=CC=1)Cl)=O VINCCSXKCFGAGE-UHFFFAOYSA-N 0.000 claims description 2
- VAOUCGFPFKRARU-UHFFFAOYSA-N 1-[11-acetyl-3-(4-cyclopropyl-2-fluorophenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-(2-ethyl-6-methylpyridin-3-yl)oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=C(C=C(C=C1)C1CC1)F)C(COC=1C(=NC(=CC=1)C)CC)=O VAOUCGFPFKRARU-UHFFFAOYSA-N 0.000 claims description 2
- YMZVBFMDDVXKCJ-UHFFFAOYSA-N 1-[11-acetyl-3-(4-cyclopropyl-2-fluorophenyl)-1,4,8,11-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-yl]-2-[2-(trifluoromethyl)pyridin-3-yl]oxyethanone Chemical compound C(C)(=O)N1CC=2N(CC1)C1=C(N=2)CCN(C1C1=C(C=C(C=C1)C1CC1)F)C(COC=1C(=NC=CC=1)C(F)(F)F)=O YMZVBFMDDVXKCJ-UHFFFAOYSA-N 0.000 claims description 2
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- YOWGRWHKDCHINP-UHFFFAOYSA-N tributyl(1,3-oxazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CO1 YOWGRWHKDCHINP-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Transplantation (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Nutrition Science (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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IB2013060243 | 2013-11-19 | ||
IBPCT/IB2013/060243 | 2013-11-19 | ||
PCT/EP2014/074887 WO2015075025A1 (fr) | 2013-11-19 | 2014-11-18 | Composés imidazole tricycliques comme inhibiteurs de la tryptophane hydrolase |
Publications (2)
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JP2016537378A JP2016537378A (ja) | 2016-12-01 |
JP6561055B2 true JP6561055B2 (ja) | 2019-08-14 |
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JP2016532102A Expired - Fee Related JP6561055B2 (ja) | 2013-11-19 | 2014-11-18 | 三環式イミダゾール化合物 |
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Country | Link |
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US (1) | US10189839B2 (fr) |
EP (1) | EP3071567B1 (fr) |
JP (1) | JP6561055B2 (fr) |
CN (1) | CN105745211B (fr) |
CA (1) | CA2927121A1 (fr) |
ES (1) | ES2650921T3 (fr) |
TW (1) | TW201609721A (fr) |
WO (1) | WO2015075025A1 (fr) |
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UA119247C2 (uk) | 2013-09-06 | 2019-05-27 | РОЙВЕНТ САЙЕНСИЗ ҐмбГ | Спіроциклічні сполуки як інгібітори триптофангідроксилази |
US9611201B2 (en) | 2015-03-05 | 2017-04-04 | Karos Pharmaceuticals, Inc. | Processes for preparing (R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanone |
WO2018177993A1 (fr) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazoles pour lutter contre les arthropodes |
CN110526878A (zh) * | 2019-09-16 | 2019-12-03 | 成都睿智化学研究有限公司 | 一种2-(噁唑基)乙胺的制备方法 |
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AU2002214505A1 (en) | 2000-11-09 | 2002-05-21 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-(4,5-c)pyridine derivatives |
JP4932135B2 (ja) * | 2002-11-22 | 2012-05-16 | 武田薬品工業株式会社 | イミダゾール誘導体、その製造法及び用途 |
WO2007089335A2 (fr) * | 2005-12-29 | 2007-08-09 | Lexicon Pharmaceutical Inc. | Derives d'acides amines multicycliques et procedes d'utilisation de ceux-ci |
UA99270C2 (en) | 2006-12-12 | 2012-08-10 | Лексикон Фармасьютикалз, Инк. | 4-phenyl-6-(2,2,2-trifluoro-1-phenylethoxy)pyrimidine-based compounds and methods of their use |
WO2014195847A2 (fr) | 2013-06-03 | 2014-12-11 | Actelion Pharmaceuticals Ltd | Nouvelle utilisation du l-tryptophane marqué par un isotope stable |
AR098436A1 (es) | 2013-11-19 | 2016-05-26 | Actelion Pharmaceuticals Ltd | Compuestos tricíclicos de piperidina |
CA2980100A1 (fr) | 2015-05-04 | 2016-11-10 | Actelion Pharmaceuticals Ltd | Composes piperidiniques tricycliques |
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2014
- 2014-11-18 ES ES14799475.0T patent/ES2650921T3/es active Active
- 2014-11-18 TW TW103139944A patent/TW201609721A/zh unknown
- 2014-11-18 EP EP14799475.0A patent/EP3071567B1/fr active Active
- 2014-11-18 CN CN201480063012.7A patent/CN105745211B/zh not_active Expired - Fee Related
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- 2014-11-18 CA CA2927121A patent/CA2927121A1/fr not_active Abandoned
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Also Published As
Publication number | Publication date |
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CN105745211B (zh) | 2017-09-26 |
US10189839B2 (en) | 2019-01-29 |
EP3071567B1 (fr) | 2017-09-06 |
TW201609721A (zh) | 2016-03-16 |
CA2927121A1 (fr) | 2015-05-28 |
WO2015075025A1 (fr) | 2015-05-28 |
US20160289232A1 (en) | 2016-10-06 |
CN105745211A (zh) | 2016-07-06 |
EP3071567A1 (fr) | 2016-09-28 |
JP2016537378A (ja) | 2016-12-01 |
ES2650921T3 (es) | 2018-01-23 |
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